Vacation Rentals in Kent County, Maryland

1. 108 Annex

Chestertown, Maryland

Welcome to 108Annex, your ideal Chesapeake Bay retreat! Nestled in historic downtown Chestertown. Just steps away from downtown restaurants, cafes, and shops, you'll be able to explore all the Arts & Entertainment District has to offer.

2. 200 High Street

Chestertown, Maryland

Bright and open 2 bedroom apartment in the heart of downtown Chestertown

3. Downtown Apartment

Chestertown, Maryland

1 Bedroom Apartment 2 blocks from downtown Chestertown MD on a quiet residential street with one queen size bed.

4. InnTowne House

Rock Hall, Maryland

Upscale, modern and new two bedroom apartment overlooking Main St. in Rock Hall. Wonderful amenities, lots of space and full kitchen. $275 per night. Up to four guests. Two night minimum, weekly rates available. Includes breakfast at Java Rock.

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1. 108 Annex

2. 200 High Street

3. Downtown Apartment

4. InnTowne House

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1. 108 Annex

2. 200 High Street

3. Downtown Apartment

4. InnTowne House

Sign up for our Tourism

E-Newsletter